Diversity-oriented synthesis of polyketide natural products via iterative chemo- and stereoselective functionalization of polyenoates: development of a unified approach for the C(1-19) segments of lituarines A-C

Amos B Smith 3rd; Shawn P Walsh; Michael Frohn; Matthew O Duffey

doi:10.1021/ol047792c

Diversity-oriented synthesis of polyketide natural products via iterative chemo- and stereoselective functionalization of polyenoates: development of a unified approach for the C(1-19) segments of lituarines A-C

Org Lett. 2005 Jan 6;7(1):139-42. doi: 10.1021/ol047792c.

Authors

Amos B Smith 3rd¹, Shawn P Walsh, Michael Frohn, Matthew O Duffey

Affiliation

¹ Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. [email protected]

PMID: 15624997
DOI: 10.1021/ol047792c

Abstract

A unified, stereocontrolled synthesis of the C(1-19) segments of the lituarines A-C (1-3) has been achieved, highlighted by application of an iterative chemo- and stereoselective trienoate functionalization protocol, a strategy that holds considerable promise for the diversity oriented synthesis of polyketides.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Biological Products / chemical synthesis*
Epoxy Compounds / chemistry*
Spiro Compounds / chemistry*
Stereoisomerism

Substances

Biological Products
Epoxy Compounds
Spiro Compounds
lituarine A
lituarine B
lituarine C

Grants and funding

CA-19033/CA/NCI NIH HHS/United States